DE1086237B - Verfahren zur Herstellung neuer 2, 5-Di-[benzimidazyl-(2')]-furan-verbindungen - Google Patents
Verfahren zur Herstellung neuer 2, 5-Di-[benzimidazyl-(2')]-furan-verbindungenInfo
- Publication number
- DE1086237B DE1086237B DEC18211A DEC0018211A DE1086237B DE 1086237 B DE1086237 B DE 1086237B DE C18211 A DEC18211 A DE C18211A DE C0018211 A DEC0018211 A DE C0018211A DE 1086237 B DE1086237 B DE 1086237B
- Authority
- DE
- Germany
- Prior art keywords
- group
- parts
- benzimidazyl
- alkyl
- new
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 9
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 7
- 239000004327 boric acid Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000005429 oxyalkyl group Chemical group 0.000 claims description 4
- 230000002152 alkylating effect Effects 0.000 claims description 3
- 239000012435 aralkylating agent Substances 0.000 claims description 3
- DNXDYHALMANNEJ-UHFFFAOYSA-N furan-2,3-dicarboxylic acid Chemical compound OC(=O)C=1C=COC=1C(O)=O DNXDYHALMANNEJ-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 1
- 238000004040 coloring Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 239000000155 melt Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CHTHALBTIRVDBM-UHFFFAOYSA-N furan-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)O1 CHTHALBTIRVDBM-UHFFFAOYSA-N 0.000 description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- DGRGLKZMKWPMOH-UHFFFAOYSA-N 4-methylbenzene-1,2-diamine Chemical compound CC1=CC=C(N)C(N)=C1 DGRGLKZMKWPMOH-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000001555 benzenes Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- SSVFMICWXDVRQN-UHFFFAOYSA-N ethanol;sodium Chemical compound [Na].CCO SSVFMICWXDVRQN-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- -1 furandicarboxylic acid Diamines Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- AGAHETWGCFCMDK-UHFFFAOYSA-N 4-methoxybenzene-1,2-diamine Chemical compound COC1=CC=C(N)C(N)=C1 AGAHETWGCFCMDK-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- GELXFVQAWNTGPQ-UHFFFAOYSA-N [N].C1=CNC=N1 Chemical group [N].C1=CNC=N1 GELXFVQAWNTGPQ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012943 hotmelt Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 238000004457 water analysis Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Lubricants (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH5463558A CH364510A (de) | 1958-01-14 | 1958-01-14 | Verfahren zur Herstellung von 2,5-Di-(benzimidazyl-(2'))-furanverbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1086237B true DE1086237B (de) | 1960-08-04 |
Family
ID=4519372
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC18211A Pending DE1086237B (de) | 1958-01-14 | 1959-01-13 | Verfahren zur Herstellung neuer 2, 5-Di-[benzimidazyl-(2')]-furan-verbindungen |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3103518A (enrdf_load_stackoverflow) |
| CH (1) | CH364510A (enrdf_load_stackoverflow) |
| DE (1) | DE1086237B (enrdf_load_stackoverflow) |
| ES (1) | ES246550A1 (enrdf_load_stackoverflow) |
| FR (1) | FR1218698A (enrdf_load_stackoverflow) |
| GB (1) | GB888209A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2522139A1 (de) * | 1974-05-23 | 1975-12-04 | Sandoz Ag | Organische verbindungen, deren herstellung und verwendung |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3147309A (en) * | 1960-09-15 | 1964-09-01 | Kali Chemie Ag | Preparation of amine-boranes |
| GB1051388A (enrdf_load_stackoverflow) * | 1964-11-17 | |||
| US3397199A (en) * | 1964-12-02 | 1968-08-13 | Smith Kline French Lab | Nitrothenylideneamino compounds |
| DE1594841A1 (de) * | 1966-01-14 | 1970-07-23 | Bayer Ag | Aufhellungsmittel |
| CH509458A (de) * | 1969-06-27 | 1971-06-30 | Ciba Geigy Ag | Verwendung von Benzofuranen zum optischen Aufhellen von Textilmaterial |
| US3940417A (en) * | 1970-12-09 | 1976-02-24 | Ciba-Geigy Corporation | Quaternised benzofuranyl-benzimidazoles |
| US3971731A (en) * | 1973-02-09 | 1976-07-27 | Bayer Aktiengesellschaft | Benzodifuran compounds |
| US4009994A (en) * | 1974-08-22 | 1977-03-01 | Ciba-Geigy Corporation | Process and product of optical brightening with quaternized benzofuranyl-benzimidazoles |
| ES467739A1 (es) * | 1977-03-16 | 1979-07-01 | Hoechst Ag | Procedimiento para la preparacion de compuestos de bisbenci-midazolil sustituidos |
| CN114591316B (zh) * | 2022-03-14 | 2024-09-20 | 黄石市利福达医药化工有限公司 | 一种2,5-双(苯并噁唑-2-)呋喃的制备方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH243782A (de) * | 1942-12-23 | 1946-07-31 | Ciba Geigy | Verfahren zur Herstellung des neuen 2,5-Di-(benzimidazyl-(2))-furans. |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2711415A (en) * | 1955-06-21 | Prepara | ||
| US2808407A (en) * | 1957-10-01 | New imidazolium compounds | ||
| US2773869A (en) * | 1954-06-21 | 1956-12-11 | American Cyanamid Co | Alkenyl bisimidazole optical bleaching agents |
-
0
- US US3103518D patent/US3103518A/en not_active Expired - Lifetime
-
1958
- 1958-01-14 CH CH5463558A patent/CH364510A/de unknown
- 1958-12-29 GB GB41935/58A patent/GB888209A/en not_active Expired
-
1959
- 1959-01-08 FR FR783532A patent/FR1218698A/fr not_active Expired
- 1959-01-13 DE DEC18211A patent/DE1086237B/de active Pending
- 1959-01-13 ES ES0246550A patent/ES246550A1/es not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH243782A (de) * | 1942-12-23 | 1946-07-31 | Ciba Geigy | Verfahren zur Herstellung des neuen 2,5-Di-(benzimidazyl-(2))-furans. |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2522139A1 (de) * | 1974-05-23 | 1975-12-04 | Sandoz Ag | Organische verbindungen, deren herstellung und verwendung |
Also Published As
| Publication number | Publication date |
|---|---|
| GB888209A (en) | 1962-01-31 |
| US3103518A (en) | 1963-09-10 |
| CH5463558A4 (enrdf_load_stackoverflow) | 1962-11-15 |
| CH364510A (de) | 1962-11-15 |
| ES246550A1 (es) | 1959-05-01 |
| FR1218698A (fr) | 1960-05-12 |
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